Acetic Acid → HCID 13763168, compound

HRID 1906719Notes

Reaction equation

HRID 1906719 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]([C:15](=O)[CH3:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25].C(O)(=O)C>CN(C)C=O.CCOCC.C(OC(C)C)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:15]([CH3:16])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25]2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 87132-AminothiophenolHCID 54493123HCID 54493123, compound

Product 1

HCID 13763168HCID 13763168, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A solution of 2-[(4-methoxyphenyl)methylene]-3-oxobutanoic acid, methyl ester (1.17 g., 5 mmole) in dimethylformamide (5 ml.) is treated with 2-aminothiophenol (695 mg., 5 mmole) and the resulting yellow solution is allowed to stir at room temperature for one hour. It is then treated with acetic acid (0.3 ml., about 5 mmoles) and the reaction is allowed to warm up to 65°. Stirring is continued at this temperature for 24 hours. After cooling to room temperature, the reaction is diluted with ether and washed with water (5×20 ml.), sodium bicarbonate, and brine, and is then dried over anhydrous magnesium sulfate. Evaporation provides a yellow foam which is dissolved in isopropyl ether and allowed to sit under refrigeration for several days. A light yellow crystalline product forms (410 mg.). Recrystallization from isopropyl ether gives an analytically pure sample of 2,5-dihydro-2-(4-methoxyphenyl)-4-methyl-1,5-benzothiazepine-3-carboxylic acid, methyl ester; m.p. 107°-109.5°. TLC (silica gel; ethyl acetate:hexane, 50:50) Rf =0.50.

Workup

  1. temperatureto warm up to 65°
  2. stirringStirring
  3. waitis continued at this temperature for 24 hours
  4. temperatureAfter cooling to room temperature
  5. washwashed with water (5×20 ml.), sodium bicarbonate, and brine
  6. dry with materialis then dried over anhydrous magnesium sulfate
  7. customEvaporation
  8. customprovides a yellow foam which
  9. waitto sit under refrigeration for several days
  10. customRecrystallization from isopropyl ether

Sources & evidence

ORD record
ord-5d39423e9ee040b19e5503fd50e6c46a
Source dataset
uspto-grants-1987_03
Patent number
US04654335

Reaction notes

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